What Has Been the Greatest Disappointment in Your Life?

Business is putting him in a bad mood
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common question asked in job interviews is, "What has been the greatest disappointment in your life?" Your response to this question will help the interviewer determine how easily you are discouraged, how you recover from difficult experiences, and whether you take responsibility for navigating challenging circumstances.

Interviewers also use this type of question to probe for failures in your personal or professional life that might reveal weaknesses that would limit your effectiveness on the job.

What the Interviewer Really Wants to Know

Interviewers ask this kind of question to understand how you perceive adversity. The way in which you moved through a tough personal situation points to your approach in professional situations as well. Employers want their team to see challenges as opportunities to learn and grow. Convince them you possess that mentality through this answer, and you will have won this round.

For example, all businesses experience ebbs and flows, and there is often a great deal of uncertainty - that is just how the business world works. If you are someone who has persevered in the most challenging and uncertain of times, then you have what it takes to help a business do the same. 

The interviewer will also note how comfortable you appear answering open-ended questions. This will speak to your ability to think quickly on your feet, as well as indicating your readiness to conduct important conversations at work.

How to Answer the “What Was Your Greatest Disappointment?” Interview Question

Employers may give you some leeway by leaving the context of your disappointment open-ended. In this case, one viable strategy is to avoid referencing a disappointment that happened at work. You could speak about a more personal disappointment, e.g., the early death of a parent, or an event that changed your academic or career goals.

If you mention a work disappointment, don't use an example that's closely related to the responsibilities of the job for which you are applying.

Believe it or not, it is also okay not to have had a "greatest" disappointment. However, in that case, provide an example of one particularly disappointing experience, or speak more generally about how you would handle a frustrating moment.

Examples of the Best Answers

My biggest disappointment is that I wasn’t able to follow my dream of being a professional dancer. I was injured as a teenager during a performance and was never able to move quite as fluidly again. Even though I was disappointed at the time, I realize now that if I had taken that direction, I would not have achieved my advanced degrees and developed a career that I love.

Why It Works: This answer shows your ability to be vulnerable and thus can help to create a strong rapport with the interviewer. It also alludes to your creativity, an attribute that is valuable in many fields. And importantly, the answer concludes on a positive note. 

I set a goal to be on the dean's list every semester in college and was very disappointed when I missed the mark during the first semester of my junior year. I was working 25 hours a week and took 21 credits that semester. I reduced my work hours to 15 and took 18 credits the next semester and achieved highest honors.

At the time, not being able to go straight to college out of high school was the greatest disappointment. However, the two years I spent working helped me to focus on what I wanted to study and ultimately made my college experience more fulfilling. Having a little extra time to figure things out allowed me to prepare to decide what I wanted to study for my chosen career.

Why It Works: The answer shows that you have a good perspective on life’s hurdles and saw this one as an opportunity to discover the things you really like, as opposed to going straight to school with little to no direction, like most high school graduates. This growth mindset is invaluable in the workplace.

I was very disappointed when I was hired for a top retailer's training program and was placed in the store management track, when I had my heart set on the buyer track. As it ends up, my strengths in employee engagement, inventory planning, and sales have enabled me to progress rapidly to my assistant store manager position, so the disappointment was a blessing in disguise. 

Why It Works: In addition to conveying who you are as a professional, it shows that you adapt to change well. In an ever-changing business world, being flexible and seeing the positives when things don’t go to plan makes the difference between collapsing and thriving when problems arise. 

Tips for Giving the Best Answer

Transition to professional from personal. This is a personal question by nature, so your answer can also be. Just remember to connect it back to the job itself. You could pivot to mentioning some key professional skills that would help you to add value if you were hired for your target job.

Choose situations which can be viewed as successes. You can respond directly to this type of question by mentioning a disappointment where you fell short of a very high expectation that you set for yourself. By doing so, you establish that you are a driven employee who strives for a high level of achievement.

Be honest. You may feel afraid to share your answer out of fear of judgment, but this question is meant to open the door to vulnerability. We all have experienced disappointment. If you're authentic about yours, it will create an answer far better than one that is made up or emotionally superficial. 

Share how you overcame the obstacle. No matter what your answer, be sure to explain how you recovered from (or how you would recover from) your disappointment. Try to emphasize how your ability to recover displays a particular quality that is important for the job. For example, if you say you were unable to afford college right after high school, explain how you worked hard over the next year to save up money. It will demonstrate your perseverance and dedication to your goals.

What Not to Say

Don’t share too much or too little information. The interviewer doesn't want to know everything about you, but disclosing too little can make him or her wonder why you aren't more open.

Avoid potentially contentious subjects such as political or religious leanings, unless you are absolutely positive that your opinions would be well-received by your interviewer. It's better to keep your views to yourself.

Don't be too negative. Try to show how you made the best of difficult circumstances rather than how terrible your disappointment was.

Possible Follow-Up Questions

Key Takeaways

BE HONEST: Don’t give a surface-level response to this personal question. Embrace being vulnerable.

TIE YOUR ANSWER TO THE JOB: Use your response to demonstrate skills and qualities that are valuable in the role.

AVOID CONTROVERSY: Don’t talk about politics, religion, or anything that could cause offense.

SHOW YOUR RESILIENCE: Explain how you bounced back and learned from the disappointment.